Ammonium formate → ethyl 6-(2,3-dihydro-1H-inden-2-ylamino)nicotinate

HRID 226446Notes

Reaction equation

Cl[C:2]1[C:3]([NH:13][CH:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH2:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:22][CH:14]1[NH:13][C:3]1[CH:2]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of ethyl 5-chloro-6-(2,3-dihydro-1H-inden-2-ylamino)nicotinate (395 mg) and ammonium formate (472 mg) in ethanol (10 mL) was added 10% palladium on carbon (40 mg), and the mixture was stirred at 100° C. for 10 hours. The catalyst in the reaction mixture was removed by filtration. The solvent was evaporated in vacuo. The residual solid was collected with hexane and ethyl acetate (2/1 v/v) to give ethyl 6-(2,3-dihydro-1H-inden-2-ylamino)nicotinate (104 mg). The mother liquid was concentrated in vacuo, and the residue was purified by preparative thin layer column chromatography (hexane/ethyl acetate=2/1) to give ethyl 6-(2,3-dihydro-1H-inden-2-ylamino)nicotinate (209 mg) as a pale yellow solid.

Workup

customThe catalyst in the reaction mixture was removed by filtration
customThe solvent was evaporated in vacuo
customThe residual solid was collected with hexane and ethyl acetate (2/1 v/v)

Sources & evidence

ORD record: ord-de2e8522374b4f8caa1df0813c65de00
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557127B2

Reaction notes

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